201541-68-6Relevant academic research and scientific papers
Design and synthesis of new [1,2,3]triazolo[4,5-d]pyrimidine derivatives as potential antiproliferative agents
Elkamhawy, Ahmed,Al-Sanea, Mohammad M.,Song, Chiman,Sim, Taebo,Roh, Eun Joo
, p. 1863 - 1873 (2015/07/15)
A new series possessing [1,2,3]triazolo[4,5-d]pyrimidine scaffold was synthesized and biologically evaluated for potential antiproliferative activity. Fourteen compounds were selected for in vitro anticancer assay over a panel of 60 cell lines at National Cancer Institute (NCI), USA. The most sensitive cell lines to the synthesized compounds were leukemia (K-562 and SR), nonsmall cell lung cancer HOP-92, and melanoma MDA-MB- 435. Compounds 12 and 24 exerted broad spectrum activity against most cell panel, while compounds 14, 21, and 23 exhibited effectiveness toward specific cell lines belong to different tumor subpanels. Accordingly, SAR, COMPARE analyses, and in silico ADME profiling were discussed for the target compounds. In addition, compounds 11 and 22 exerted good FGFR3 inhibitory activity with 58.8 and 46.7% at 100 μM, respectively. Taken as a whole, the present study revealed that the new series can be considered as promising lead for further development of more potent anticancer agents as well as FGFR3 kinase potential inhibitors.
1,2,3-Triazolo[4,5-e]-1,2,4-triazolo[3,4-c]pyrimidines
Biagi, Giuliana,Giorgi, Irene,Livi, Oreste,Manera, Clementina,Scartoni, Valerio
, p. 1195 - 1198 (2007/10/03)
Some new 1,2,3-triazolo[4,5-e]-1,2,4-triazolo[3,4-c]pyrimidines were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyrimidines via the formation of the 1,2,4-triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate to give the expected tricyclic derivatives 7, 8 and 9. Intramolecular cyclization of the ethoxycarbonylhydrazino derivatives 10 gave the tricyclic compounds 11 bearing an hydroxyl group in the 3 position. The v-triazolo-s-triazolopyrimidine derivatives were tested towards the A1 and A(2A) adenosine receptors in binding assays, but they did not show any receptor affinity.
Novel 3-aralkyl-7(amino-substituted)-1,2,3-triazolo[4,5-d]pyrimidines with high affinity toward A1 adenosine receptors
Betti, Laura,Biagi, Giuliana,Giannaccini, Gino,Giorgi, Irene,Livi, Oreste,Lucacchini, Antonio,Manera, Clementina,Scartoni, Valerio
, p. 668 - 673 (2007/10/03)
Three series of several 1,2,3-triazolo[4,5-d]pyrimidine derivatives bearing various amino substituents at the 7 position and one of three lipophilic substituents at the 3 position (benzyl, phenethyl, or 2- chlorobenzyl) were prepared starting from the corresponding 7-chloro compounds, by nucleophilic substitution by the appropriate amine. Radioligand binding assays at bovine brain adenosine A1 and A(2A) receptors showed that some compounds possessed a high affinity and selectivity for the A1 receptor subtype. In particular the biological results suggested the compounds bearing cycloalkylamino (cyclopentyl- and cyclohexylamino) or aralkylamino (α- methylbenzyl- and 1-methyl-2-phenylethylamino or amphetamino) substituents at the 7 position were the most active derivatives. The best lipophilic substituent at the 3 position was the 2-chlorobenzyl (A1 affinity K(i) 1 receptor affinity. These facts allowed us to attribute to these molecules a binding mode within the A1 adenosine receptor analogous to that of the corresponding triazolopyridazines.
